The band were originally based in Whitstable, Kent, near Canterbury, but moved to London when briefly signed to Verve Records. After being dropped by Verve, the band signed to Decca Records, where they released their most critically acclaimed album, In the Land of Grey and Pink in 1971. David Sinclair left after the album's release and the group split up the following year. Hastings and Coughlan added new members, notably viola player Geoffrey Richardson, continuing on before splitting in 1978.

The band reformed several times in the following decades, and Caravan still remain active as a live band in the 21st century, despite Coughlan's death in December 2013.

The group's original members, David Sinclair, Richard Sinclair, Pye Hastings and Richard Coughlan had all been in the Canterbury-based Wilde Flowers, albeit not at the same time. Richard Sinclair had been an early member, but left in September 1965 to study at college.[2] Hastings had replaced Robert Wyatt as the group's singer and Coughlan as drummer in the band when Wyatt, who performed both roles, formed Soft Machine.[3] David Sinclair joined the group in late 1966, but after future Soft Machine member Hugh Hopper left the group in June the following year, they began to run out of momentum and broke up in October 1967.[4]

Coughlan, Hastings and the two Sinclairs subsequently formed Caravan in 1968. "We all had the same goal" recalled Richard Sinclair, "to make our music, write it ourselves, and make a living from it."[5] The band rented a house in Whitstable, Kent for six months, where they began to write and rehearse new material.[6] They also borrowed Soft Machine's PA for rehearsals while that band was on tour with Jimi Hendrix in the US, as Caravan did not have enough funds for their own equipment.[7] They were forced to leave in June and ended up living in tents and rehearsing in a local church hall.[6] By October, they had attracted the interest of music publicist Ian Ralfini,[8]:4 who signed them to the American record label, Verve Records, and became the first British act they signed.[6] Verve subsequently released the band's debut LP, Caravan (1968), later the same year, but a few months later moved out of the UK record business and dropped the band.[8]:3

Caravan had started to build a live following by mid-1970, including an appearance at the Kralingen Pop Festival in the Netherlands to an audience of 250,000 and the 10th Plumpton Festival. In autumn 1970, Caravan began working on one of their most critically acclaimed albums, In the Land of Grey and Pink (1971). The balance of songwriting changed from the previous two albums, with Richard Sinclair taking a more prominent role. His song, "Golf Girl" was originally written about his then girlfriend (and future wife), but the lyrics were rewritten in the final version.[9]:8 The group decided to follow up "For Richard" with a suite of short sections of songs written by David Sinclair, that the rest of the band worked on and linked together to form a side-long track, "Nine Feet Underground". Although, the track was recorded in five separate stages and spliced together, the band performed the suite live as it was finally presented on the album, and it remained a popular track in their live set.[9]:9 The album was released in April 1971, and though it did not chart, it has remained in print ever since, and has been remastered for CD several times,[9]:10 notably a digital remaster in 2011 by Porcupine Tree's Steven Wilson.[10] "Nine Feet Underground" in particular was a regular fixture on late-night FM radio during the early 1970s.[11]

Despite the critical success of In the Land of Grey and Pink, the group were disappointed by its lack of commercial success, believing that Decca were not promoting the band properly or investing enough money. In August 1971, David Sinclair accepted a job with former Soft Machine drummer Robert Wyatt's new band, Matching Mole. Reflecting on the decision to leave, Sinclair later said "I felt the whole thing was going a bit stagnant ... I wanted to play with other people, but had to accept that with Caravan it was either all or nothing."[9]:11 Hastings remembers that "Dave's departure was a serious blow."[12]:5

The remaining members continued on together and Richard Sinclair invited keyboardist Steve Miller to join the band.[12]:5 However, it was immediately apparent that the style of the band would be different. Sinclair and Miller wanted to perform more jazz-rock, while Hastings was frustrated that the previous style was being neglected, and that it was "virtually impossible" to get Miller to perform in David Sinclair's style.[12]:8 The band started recording a new album, Waterloo Lily (1972) in late 1971, which was the first use of orchestral instrumentation, arranged by Hastings and his brother, Jimmy, who had guested on previous albums.[12]:9 The album was released in May 1972, but by this time, musical differences had come to a head, and after a gig with Genesis in July, the band split. Richard Sinclair later said, "It didn't quite work with Steve in the band because the music started to go a bit too loose for the way that Pye and Richard Coughlan played."[12]:10

Hastings and Coughlan decided to continue as Caravan, and the duo recruited viola player Geoffrey Richardson, bassist Stu Evans and keyboardist Derek Austin and toured extensively. This line-up did not make any recordings before Evans was replaced by John G. Perry and Dave Sinclair rejoined the group in 1973.[1]

The resulting album For Girls Who Grow Plump in the Night (1973) was a major critical achievement[1] and showed that the group could survive the loss of co-vocalist Richard Sinclair. Jimmy Hastings reprised his role as orchestrator along with Martyn Ford and John Bell,[13] while the Soft Machine's Mike Ratledge contributed an instrumental piece, "Backwards" as part of a medley.[14] The group followed this with a live album, Caravan and the New Symphonia (1974), including orchestral arrangements by Ford[15] and conducting by Simon Jeffes.[13]

Perry left after the New Symphonia and was replaced by Mike Wedgwood for the album Cunning Stunts (1975), which reached the top 50 in the UK[16] and was a minor hit in the US, reaching number 124.[1] It was the last album released on Decca, which preceded a number of other problems in the band. David Sinclair left after the album was recorded and was replaced by Jan Schelhaas, with the band's sound becoming more mainstream.[13] The group signed to Miles Copeland's BTM Records[1] and recorded Blind Dog at St. Dunstans (1976) which was another minor album hit,[17] but by this point the group were out of step with the prevailing musical trends, and after a final album, Better by Far (1977) on Arista Records,[1] the group split.[13]

Pye Hastings performing with Caravan at the High Voltage Festival in 2011

Caravan were largely dormant in the 1980s until a 1990 reunion, planned as a one-off for television, reinvigorated their career.[13] The group continued to tour in the early 1990s, before Richard Sinclair left. He was replaced by Jim Leverton, while Geoffrey Richardson rejoined the band. This version of the group released The Battle of Hastings in 1995.[13]

In 2010, Pye Hastings announced that the band had resumed activity in anticipation of a one-off concert recording at Metropolis Studios for ITV, which took place in December 2010. New material was written for a debut performance and the band was joined by Mark Walker on drums and percussion, as Richard Coughlan, whilst still a member of the band, was too ill to tour with the group.[19] The DVD of this gig was released in May 2011 and the recording was shown on ITV as part of the Legends series.[20]

In January 2013, the band completed a successful UK tour to celebrate the 40th Anniversary of the album For Girls Who Grow Plump in the Night (1973).[21] This was followed later in the year by the announcement of a new album, Paradise Filter (2013). The album was funded by a PledgeMusic campaign, scheduled for release on 24 February 2014. Hastings declared "now you can be part of the whole process by pledging to support this project".[22]

On 1 December 2013, founding member Coughlan died, having been in poor health for some years.[19][23] His funeral took place in Canterbury on 20 December. A statement from the band stated "his unique style of playing and wonderful character will be sorely missed."[24]

Caravan headlined the RoSfest festival in Pennsylvania, USA from 2–4 May 2014.

Caravan are considered a key example of the Canterbury scene genre.[25] Their records generally indicate a jazz influence, and the group's lyrics have been described as whimsical and very "English", particularly during Richard Sinclair's tenure in the band.[26] Following Sinclair's departure, the musical direction has been predominantly led by Pye Hastings, who preferred a softer pop rock approach.[14] Though the group share a common history with Soft Machine, they have been considered more melodic and closer to folk music[27] and frequently displaying a sense of humour. The group were predominantly album-oriented, but Hastings believes the group recorded enough straightforward pop that could have been hit singles if the record company had taken sufficient interest.[28]

Instrumentally, David Sinclair's fuzztone Hammond organ sound is a key ingredient of the early Caravan albums,[25] and his playing is the dominant instrument on them.[26] His musical palette subsequently expanded to include synthesizers.[14] Jimmy Hastings' woodwind playing and orchestral arrangements have also been a regular feature in the band's music since its inception.[12]:9